Chief Product Officer

Trolley • Montreal, QC

11d • Hybrid

About The Position

Trolley is the payouts platform for the internet economy, aiming to unlock global economic opportunity through a borderless payouts ecosystem. Their platform and API enable businesses to pay people worldwide, supporting creators, on-demand workers, and suppliers at scale. Companies use Trolley for automated payouts, tax and banking information collection, and fraud/risk reduction. As Trolley enters a new growth phase, they are heavily investing in AI to drive product innovation, enhance customer experiences, and solidify their market leadership. They are seeking a Chief Product Officer (CPO) to define the product vision, shape long-term strategy, and lead platform evolution. The CPO will be a key member of the Executive Leadership Team, responsible for defining and executing the company's product vision, strategy, and roadmap. The ideal candidate will have extensive experience building and scaling enterprise B2B SaaS products in fintech, payments, financial infrastructure, embedded finance, or banking technology. They must understand the complexities of building mission-critical financial products where customer experience, regulatory compliance, security, and reliability are paramount. Working closely with the CTO, the CPO will ensure Trolley continues to develop products that address significant customer challenges, enhance their competitive standing, and foster sustainable growth. While the CTO manages technology strategy, engineering, architecture, AI enablement, and Information Security, the CPO is accountable for product vision, customer value, product strategy, and commercial success across the platform. The CPO will lead Product Management and Product Design, collaborating with Engineering, Customer Success, Sales, Marketing, Compliance, Finance, Operations, and Risk. A primary focus will be defining how AI can create distinct customer value through intelligent automation, workflow optimization, and innovative product capabilities that improve the speed, confidence, and efficiency of global money movement.

Requirements

• 10+ years of progressive product leadership experience, including leading Product Management organizations.
• Experience as a Chief Product Officer, VP Product, SVP Product, VP Product Management or equivalent executive within a high growth fintech, payments, financial infrastructure, embedded finance, or banking technology company.
• Demonstrated experience building and scaling enterprise B2B products within the payments ecosystem is required.
• Deep understanding of payment processing, cross border payments, money movement, payment operations, financial APIs, and platform based software products.
• Proven experience defining product strategy and delivering products that drive measurable customer and business outcomes.
• Experience building products within highly regulated environments where compliance, security, privacy, and reliability are essential.
• Strong experience partnering with Engineering organizations to deliver complex, API first software platforms.
• Demonstrated success leading cross functional organizations through rapid growth and organizational change.
• Proven ability to recruit, develop, and retain high performing Product Management and Product Design teams.
• Exceptional strategic thinking, executive communication, and stakeholder management skills.

Nice To Haves

• Experience with payout infrastructure, payment orchestration, merchant services, or embedded finance.
• Experience building products involving tax reporting, KYC/KYB, fraud prevention, identity verification, treasury, or financial operations.
• Experience leading enterprise API platforms.
• Experience launching AI-powered customer-facing products.
• Experience scaling globally distributed product organizations.

Responsibilities

• Define and execute Trolley's long-term product vision and strategy.
• Own and prioritize the company-wide product roadmap.
• Align product investments with company strategy, customer needs, and commercial priorities.
• Identify opportunities to expand Trolley's platform, strengthen competitive differentiation, and enter adjacent markets.
• Balance innovation, customer requests, regulatory requirements, and technical investment to maximize long-term value.
• Partner with the CEO and Executive Leadership Team to shape company strategy.
• Define product strategy across global payouts, tax, compliance, APIs, financial workflows, and future platform capabilities.
• Build products that simplify complex global payment operations while maintaining the highest standards of security, compliance, and reliability.
• Drive product discovery through customer research, market analysis, competitive intelligence, and data.
• Champion continuous experimentation, customer validation, and iterative product development.
• Ensure Trolley remains at the forefront of innovation within the global payments ecosystem.
• Define Trolley's long-term AI product strategy.
• Identify opportunities to embed AI throughout the customer journey.
• Prioritize AI capabilities that improve onboarding, fraud detection, compliance, reporting, customer support, operational efficiency, and user productivity.
• Partner closely with the CTO to bring AI-powered capabilities to market.
• Ensure AI features deliver measurable customer value while maintaining responsible and secure AI practices.
• Build, develop, and lead world-class Product Management and Product Design teams.
• Establish product operating rhythms, roadmap planning processes, and product governance.
• Create a culture centered on customer obsession, accountability, innovation, collaboration, and execution.
• Recruit, mentor, and develop exceptional product leaders.
• Define success metrics that measure product adoption, customer satisfaction, retention, expansion, and business impact.
• Serve as the executive team voice of the customer.
• Build strong relationships with strategic customers, partners, and industry stakeholders.
• Maintain deep expertise across fintech, payments, embedded finance, financial infrastructure, and regulatory trends.
• Translate customer feedback, industry developments, and competitive insights into product strategy.
• Partner closely with Sales, Marketing, and Customer Success on pricing, packaging, positioning, product launches, and customer adoption.
• Serve as a trusted advisor to the CEO and Board on product strategy, customer needs, market opportunities, and competitive positioning.
• Partner closely with the CTO to ensure product strategy and technology strategy evolve together.
• Contribute to company-wide strategic planning and operational excellence.
• Represent Trolley with customers, partners, investors, analysts, and industry events.
• Help shape the future direction of the company as a member of the Executive Leadership Team.

Benefits

• Competitive salary & annual Leadership bonus.
• ESOP Program: Meaningful equity and ownership that aligns your success with ours.
• Extended healthcare benefits from Day 1.
• 4 weeks paid vacation per year + public holidays (+1 extra vacation day per year of service).
• 30 days remote work from anywhere.
• Gym membership allowance.
• 1/2 day Fridays off during summer.
• Company-provided use of Apple MacBook Pro and Mac gear.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed